KR20150086681A - Cosmetic composition for promoting a differentiation of adipocyte comprising hydroxy pyranone derivative - Google Patents

Abstract

The present invention relates to an adipocyte differentiation promoting composition containing hydroxymethyl pyranone derivatives as active ingredients. According to the present invention, the composition can promote the adipocyte differentiation to enable the adipocytes in a skin layer to be differentiated to enhance the volume and elasticity of the skin. The composition can also be utilized as a cosmetic or pharmaceutical composition in various fields including the skin damage treatment.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a cosmetic composition for promoting differentiation of adipocytes comprising a hydroxypyranone derivative compound,

The present invention relates to a cosmetic composition for promoting adipocyte differentiation.

The basic structure of the skin is maintained by subcutaneous fat tissue, and this subcutaneous fat tissue plays a role in the volume and intensity of the skin. Therefore, as mentioned above, increasing the volume of the fat tissue rather than imparting elasticity to the dermis or epidermis in the outer skin layer, which has been used previously, may be a good solution to maintain the volume and elasticity of the skin. Studies using adipocytes have been actively conducted in various fields. Generally used preadipocytes are widely used cells because they have the property of differentiating into adipocytes by differentiation inducers such as insulin. Mesenchymal stem cells are recently attracting attention in research using these adipocytes. Since adipose-derived mesenchymal stem cells can be differentiated using methods similar to those used to differentiate adipocyte precursor cells into adipocytes (Exp. Cell Res. 2006, 312, 1856-1864), adipocyte differentiation studies (Science 1999, 284, 143-146). It is known that these adipose-derived mesenchymal stem cells can be differentiated not only into adipocytes but also into other types of cells such as chondrocytes and bone cells (J. Cell Sci. 2006 119, 2204-2213) Is distributed.

KR10-2013-0107865A

Exp. Cell Res. 2006, 312, 1856-1864 Science 1999, 284, 143-146 J. Cell Sci. 2006 119, 2204-2213

Accordingly, the inventors of the present invention confirmed that a compound having a specific structure promotes adipocyte differentiation among hydroxypyranone derivatives during a study on compounds exhibiting adipocyte differentiation promotion effect, and completed the present invention.

Accordingly, an object of the present invention is to provide a composition for stimulating adipocyte differentiation, skin volume or elasticity-enhancing composition comprising such a hydroxypiranone derivative compound.

In order to achieve the above object, the present invention provides a composition for promoting differentiation of adipocytes, a skin volume or an elasticity-enhancing composition comprising a hydroxypiranone derivative as an active ingredient.

The composition according to the present invention contains a hydroxypiranone derivative as an active ingredient and exhibits an effect of promoting the differentiation of adipocytes, thereby exhibiting an effect of increasing the volume or elasticity of the skin. More specifically, it promotes the differentiation of human mesenchymal stem cells into adipocytes, thereby producing a lipid droplet, thereby increasing the volume and elasticity of the skin. Accordingly, the composition of the present invention can be utilized variously in the field of cosmetics or pharmaceuticals.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a microscopic photograph showing the results of induction of adipocyte differentiation of a hydroxypiranone derivative compound according to the present invention. FIG.

In one aspect, the present invention relates to a skin volume or elasticity-enhancing composition comprising, as an active ingredient, a hydroxypiranone derivative compound represented by the following formula (1):

[Chemical Formula 1]

In the formula, R is -CH ₂ -, or -CH ₂ CH ₂ - Im.

In one aspect of the present disclosure, a composition according to the present disclosure may be one which promotes the differentiation of mesenchymal stem cells into adipocytes.

In one aspect of the present disclosure, the mesenchymal stem cells may be human mesenchymal stem cells.

In one aspect of the present disclosure, a composition according to the present disclosure may have a concentration of active ingredient of from 0.01 μM to 100 μM based on the total volume of the composition. Also in one aspect of the present disclosure, the concentration of the active ingredient is at least 0.001 M, at least 0.01 M, at least 0.1 M, at least 0.5 M, at least 1 M, at least 5 M, at least 10 M, at least 20 M, at least 25 M At least 30 μM, at least 30 μM, at least 31 μM, at least 32 μM, at least 35 μM, at least 40 μM, at least 50 μM, at least 100 μM, at least 200 μM, at least 500 μM, at least 1 mM, at least 10 mM, at least 50 mM, It may be 5M or more and may be 10M or less. In one aspect of the present disclosure, the concentration of the active ingredient may preferably be 30 [mu] M.

In one aspect of the present disclosure, a composition according to the present disclosure may be characterized as increasing fat tissue.

In one aspect of the present disclosure, a composition according to the present disclosure may be characterized by increasing skin volume.

In one aspect of the present disclosure, the composition according to the present disclosure may be characterized as increasing skin elasticity.

In one aspect of the present disclosure, the composition according to the present disclosure may be a pharmaceutical, food or cosmetic composition.

According to an aspect of the present invention, there is provided a process for preparing a hydroxypiranone derivative represented by Formula 1,

(1) 5-hydroxy-2- (chloromethyl) -4H-pyran-4-one is obtained by replacing the hydroxy group of the hydroxymethyl group at the 2-position of 5-hydroxy- -4H-pyran-4-one;

(2) reacting 3,4-methylenedioxinic acid or 3,4-ethylenedioxinic acid with an inorganic base in a polar solvent to prepare a metal salt; And

(3) reacting the 5-hydroxy-2- (chloromethyl) -4H-pyran-4-one with the metal salt.

The preparation method according to the above method will be described with reference to Reaction Scheme 1 below.

[Reaction Scheme 1]

In the formula, R is -CH ₂ -, or -CH ₂ CH ₂ - is.

Specific examples of the hydroxypiranone derivative compound of the formula (1) obtained by the process according to the present invention include (2E) - (5-hydroxy-4-oxo-4H- yl) acrylate and (2E) - (5-hydroxy-4-oxo-4H-pyran- Hydroxybenzo [b] [1,4] dioxo-7-yl) acrylate.

In one aspect, the present specification may relate to a skin volume or elasticity-enhancing composition comprising a hydroxypiranone derivative compound prepared by the manufacturing method according to the present invention as an active ingredient.

The hydroxypiranone derivative compound represented by the formula (1) produced by the manufacturing method according to the present invention can promote and accelerate the differentiation of adipocytes, thereby generating and accumulating lipid spheres. Therefore, it is possible to improve the elasticity of the skin and improve the volume of the skin have.

In one aspect, the present invention provides a composition for promoting adipocyte differentiation,

The present invention relates to a composition for promoting differentiation of adipocytes comprising a hydroxypyran derivative represented by the following formula (1) as an active ingredient.

[Chemical Formula 1]

In the formula, R is -CH ₂ -, or -CH ₂ CH ₂ - Im.

As used herein, the term "skin" refers to an organ covering the outside of an organism, which is composed of epidermis, dermis and subcutaneous fat layer and includes not only a tissue covering the outside of the face or the whole body, to be.

As used herein, the term "volume " refers to volume, volume, or volume of the surface or inside of the skin layer and may mean a bulky feeling exposed to the outer surface. Thus, in the case of a volume that is swollen or promoted, the apparent shape will be firm, healthy and young. In addition, there is a risk that the skin may be damaged due to external injuries, trauma, burns, or the like, scars resulting therefrom, dents on the outer surface of the skin, incisions on the skin or tissue due to surgery, When the volume is increased, the volume of the tissue and the skin layer of the damaged part is increased, and the skin or tissue is restored to be close to the original state.

As used herein, the term "volume enhancement" means that the volume of the skin layer is increased or increased, or the shape of the skin surface means that the sense of volume is enhanced and tightened and looks healthy, or the damaged skin tissue is restored, It can mean something. Therefore, when the volume of the skin tissue is increased, the volume of the increased skin layer is increased and the surface of the skin is spread together to increase the volume of the damaged skin tissue, thereby increasing the volume of the skin layer and bringing the skin closer to the original state C.

The formulation of the cosmetic composition according to one aspect of the present invention is not particularly limited and can be appropriately selected according to the purpose. For example, skin lotion, skin softener, skin toner, astringent, lotion, milky lotion, moisturizing lotion, nutrition lotion, massage cream, nutritional cream, moisturizing cream, hand cream, foundation, essence, nutrition essence, pack, soap, cleansing But the present invention is not limited thereto, and may be manufactured by any one or more formulations selected from the group consisting of a foam, a cleansing lotion, a cleansing cream, a body lotion and a body cleanser.

Starch, tragacanth, cellulose derivatives, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide as the carrier component when the formulation of the cosmetic composition according to the present invention is a paste, cream or gel. Etc. may be used.

When the formulation of the cosmetic composition according to the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as a carrier component, Propellants such as hydrocarbons, propane / butane or dimethyl ether.

When the formulation of the cosmetic composition according to the present invention is a solution or emulsion, a solvent, a solvent or an emulsifier is used as a carrier component, and examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, Propylene glycol, 1,3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol or fatty acid esters of sorbitan.

In the case where the formulation of the cosmetic composition according to the present invention is a suspension, a carrier liquid such as water, a liquid diluent such as ethanol or propylene glycol, a suspension such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester , Microcrystalline cellulose, aluminum metahydroxide, bentonite, agar or tracant, etc. may be used.

In the case of the surface-active agent-containing cleansing of the cosmetic composition according to the present invention, as the carrier component, aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyltaurate, sarcosinate, Fatty acid amide ether sulfate, alkylamidobetaine, aliphatic alcohol, fatty acid glyceride, fatty acid diethanolamide, vegetable oil, linolenic derivative or ethoxylated glycerol fatty acid ester.

The cosmetic composition according to the present invention may further contain, in addition to the hydroxypiranone derivative compound, a functional additive and a component included in a general cosmetic composition. The functional additives may include water-soluble vitamins, oil-soluble vitamins, polymer peptides, polymeric polysaccharides, sphingolipids and seaweed extracts.

The cosmetic composition of the present specification may further contain, in addition to the above-described functional additive, components contained in a general cosmetic composition as required. Examples of the other ingredients that can be included in the composition include humectants, emollients, surfactants, organic and inorganic pigments, organic powders, ultraviolet absorbents, preservatives, bactericides, antioxidants, plant extracts, pH adjusters, alcohols, Accelerators, coolants, antiperspirants, purified water, and the like.

Further, the present invention relates to a skin external preparation comprising a hydroxypiranone derivative compound as an active ingredient, wherein the external preparation for skin is a generic term including any substance applied outside the skin, and various cosmetic formulations may be included therein have.

The pharmaceutical compositions according to the present disclosure may be of various oral or parenteral formulations. In the case of formulation, a diluent or excipient such as a filler, an extender, a binder, a wetting agent, a disintegrant, or a surfactant is usually used. Solid form preparations for oral administration include tablets, pills, powders, granules, soft or hard capsules, etc. These solid preparations may contain one or more excipients such as starch, calcium carbonate, sucrose, Or lactose, gelatin, and the like. In addition to simple excipients, lubricants such as magnesium stearate, talc, and the like are also used. Liquid preparations for oral administration include suspensions, solutions, emulsions, syrups and the like. Various excipients such as wetting agents, sweeteners, fragrances, preservatives and the like may be included in addition to water and liquid paraffin, which are simple diluents commonly used. have. Formulations for parenteral administration include sterilized aqueous solutions, non-aqueous solutions, suspensions, emulsions, freeze-dried preparations, and suppositories. Propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like can be used as the non-aqueous solvent and suspension agent. Examples of the suppository base include witepsol, macrogol, tween 61, cacao paper, laurin, glycerogelatin and the like.

The pharmaceutical dosage forms of the compositions herein may be used in the form of their pharmaceutically acceptable salts and may also be used alone or in combination with other pharmaceutically active compounds, as well as in a suitable set. The salt is not particularly limited as long as it is pharmaceutically acceptable so long as it is pharmaceutically acceptable and includes, for example, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrofluoric acid, hydrobromic acid, formic acid acetic acid, tartaric acid, lactic acid, citric acid, fumaric acid, , Benzenesulfonic acid, toluenesulfonic acid, and naphthalenesulfonic acid.

The composition of the present invention may be administered parenterally or orally, and may be administered in one to several divided doses in an amount of 0.1 to 500 mg, preferably 1 to 100 mg per kg of body weight per day have. The dosage for a particular patient may vary depending on the patient's body weight, age, sex, health condition, diet, time of administration, administration method, excretion rate, severity of disease, and the like.

The pharmaceutical composition according to the present invention may be formulated into various forms such as powders, granules, tablets, soft or hard capsules, oral formulations such as suspensions, emulsions, syrups and aerosols, external preparations such as ointments and creams, suppositories, And sterile injection solutions. The pharmaceutical composition may be formulated in any form suitable for pharmaceutical preparations, preferably in the form of injections or skin external preparations.

The compositions according to the present disclosure can be administered to mammals such as rats, mice, livestock, humans, and the like in a variety of routes including parenterally, orally, and all manner of administration can be expected, for example, Or by intravenous, intramuscular, subcutaneous, intramural or intracerebroventricular injection.

Compositions according to the present disclosure can be administered by a variety of routes, which are readily applicable to those of ordinary skill in the art. In particular, the pharmaceutical composition according to the present invention can be administered by a route applied to the skin surface as an external preparation for skin.

In one aspect of the present disclosure, the food composition may be a health functional food composition.

The formulation of the food composition according to the present specification is not particularly limited, but may be formulated into, for example, tablets, granules, powders, liquid preparations such as a drink, caramels, gels, bars and the like. The food composition of each formulation can be blended with the ingredients commonly used in the field in addition to the active ingredient without difficulty by those skilled in the art depending on the purpose of formulation or use, and synergistic effect can be obtained when the composition is applied simultaneously with other ingredients.

In the food composition according to the present specification, the dosage determination of the active ingredient is within the level of those skilled in the art, and its daily dosage is, for example, from 0.1 mg / kg / day to 5000 mg / kg / day, mg / kg / day to 500 mg / kg / day, but it is not limited thereto, and may vary depending on various factors such as the age, health condition, and complication of the subject.

The food composition according to the present invention may be used as a food or beverage such as various foods such as chewing gum, caramel product, candy, ice cream, confectionery, beverage such as soft drink, mineral water, alcoholic beverage, healthful food including vitamins and minerals .

In addition to the above, the food composition which is one aspect of the present invention may be in the form of a flavoring agent such as various nutrients, vitamins, minerals (electrolytes), synthetic flavors and natural flavors, colorants and enhancers (cheese, chocolate etc.), pectic acid and its salts, Alginic acid and its salts, organic acids, protective colloid thickeners, pH adjusting agents, stabilizers, preservatives, glycerin, alcohols, carbonating agents used in carbonated drinks and the like. In addition, the functional food compositions of the present disclosure may include natural fruit juice and pulp for the production of fruit juice drinks and vegetable drinks. These components may be used independently or in combination. The proportion of such additives is not so critical, but is generally comprised in the range of 0 to about 20 parts by weight per 100 parts by weight of the composition herein.

Hereinafter, the configurations and effects of the present invention will be described in more detail with reference to examples and test examples. However, these examples and test examples are provided for illustrative purposes only in order to facilitate understanding of the present specification, and the scope and range of the present specification are not limited by the following examples.

Example 1 Synthesis of (2E) - (5-hydroxy-4-oxo-4H-pyran-2-yl) methyl 3- (benzo [d] [1,3] dioxo- Produce

(0.35 mmol) of 5-hydroxy-2- (hydroxymethyl) -4H-pyran-4-one (0.35 mmol) was dissolved in 250 ml of N, N-dimethylformamide, cooled in an ice- 0.42 mol) was added dropwise over 30 minutes. After stirring at room temperature for 2 hours, the reaction solution was added to 2000 ml of ice water. The resulting solid was filtered, and a solid (filtrate) was dissolved in 1000 ml of ethyl acetate. Magnesium sulfate and activated charcoal were added, dried, discolored and filtered, and the filtrate was concentrated and nucleic acid was added to obtain crystals. And dried in vacuo to obtain 39.5 g (70%) of the reaction product, 5-hydroxy-2- (chloromethyl) -4H-pyran-4-one as a yellow solid.

5 g (0.026 mol) of 3,4-methylenedioxininnamic acid and 1.3 g (0.031 mol) of sodium hydroxide were dissolved in 40 ml of methanol. The methanol was distilled off and the residue was dissolved in 70 ml of N, N-dimethylformamide. 4.2 g (0.026 mol) of 5-hydroxy-2- (chloromethyl) -4H-pyran-4-one was added and the mixture was heated and stirred in an oil bath at 110 ° C for 2 hours. The solvent was distilled off and the residue was dissolved in 300 ml of ethyl acetate. The ethyl acetate solution was washed with 5% hydrochloric acid and distilled water, dried over magnesium sulfate and activated carbon, and discolored. Insolubles were filtered off and the filtrate was evaporated under reduced pressure (12 torr) to give 5.3 g (65% yield) of the reaction product as a off-white solid.

TLC (ethyl acetate: hexane = 1: 1) Rf = 0.63

¹ H NMR (DMSO-d 6,?): 9.29 (bs, 1H), 8.12 (s, 1H), 7.65 (d, 1H, J = 16.2 Hz), 7.46 2H, J = 8.1 Hz), 6.96 (d, IH, J = 8.1 Hz), 6.60 (d, IH, J = 16.2 Hz), 6.52 (s, .

Example 2 (2E) - (5-Hydroxy-4-oxo-4H-pyran-2-yl) methyl 3- (2,3-dihydroxybenzo [b] [1,4] 7-yl) acrylate

The title compound (5.0 g, 57%) was obtained as an off-white solid in the same manner as in Example 1, except that 3,4-ethylenedioxinnamic acid was used instead of 3,4-methylenedioxininnamic acid.

TLC (ethyl acetate: hexane = 1: 1) Rf = 0.58

^{1 H NMR (DMSO-d6,} δ): 9.26 (bs, 1H), 8.11 (s, 1H), 7.63 (d, 1H, J = 16.2Hz), 7.32 (s, 1H), 7.25 (d, 1H, J = 8.1 Hz), 6.90 (d, 1H, J = 8.1 Hz), 6.59 (d, 1H, J = 16.2 Hz), 6.51 (s, .

[Experimental Example 1] Experiment on adipocyte differentiation induced by adipose tissue derived mesenchymal stem cell

Human adipose tissue derived mesenchymal stem cells (hAT-MSCs) were purchased from Lonza, Inc. (Walkersville, MD, USA) and cultured according to Lonza's guidelines. Adipocyte differentiation was carried out using a method recommended by Ron, except that troglitazone (TRO) was used instead of indomethacin to induce adipocyte differentiation of adipose derived mesenchymal stem cells. Specifically, mesenchymal stem cells are differentiated into adipocytes by inserting 1 g / ml of insulin, 1 M of dexamethasone (DEXA), 0.5 mM of isobutylmethylxanthine (IBMX) and 2 M of TRO into the culture medium of mesenchymal stem cells . For the experimental group, a concentration of 30 μM of the compound of Example 1 was added to the medium upon induction of adipocyte differentiation. As a positive control group, glibenclamide (30 μM) was treated with IDX medium. After 14 days from the start of adipocyte differentiation of adipose-derived mesenchymal stem cells, the cell culture medium was removed and the cells were washed with 10 ml of phosphate buffered saline (PBS). The cells were washed with 10% formalin / PBS solution 0.2 ml / cm < ² > for 10 minutes. The immobilized cells were washed once with a 60% isopropanol solution 0.5 ml / cm ² , and then stained with 0.2 ml / cm ² of a dye-containing solution of Oil-Red-O in 60% isopropanol for 10 minutes Lipid bodies were stained. Subsequently, re-staining was performed with hematoxylin to make it easy to distinguish the nucleus and then observed with a microscope. The results are shown in Fig.

1, it can be seen that the treatment of the compound of Example 1 showed an increase in the differentiation of adipocytes rather than treatment of IDX cells, and compared with the positive control group of glibenclamide, the number of stained cells was rather small, Which is a significant increase. Therefore, it has been confirmed that the hydroxypiranone derivative compound according to the present invention or the composition containing the same exhibits an effect of promoting differentiation of adipocytes, and thus shows an effect of promoting skin volume or elasticity.

[Test Example 2] Measurement of adiponectin expression level of human adipose derived mesenchymal stem cells

Adiponectin is a typical protein hormone secreted by adipocytes. Such adiponectin has been reported to increase its expression as adipocytes differentiate. Thus, the amount of adiponectin, which is an index of promotion of adipocyte differentiation, was secreted into a cell culture medium. Adiponectin ELISA kit (R & D systems, cat. ≪ / RTI > cat) was used to measure adiponectin secretion level. Adipose tissue derived mesenchymal stem cells were purchased from Lonza Corporation. No. DY1065) was used to quantify the amount of adiponectin (each data value corrected for control). The specific measurement method using the adiponectin ELISA kit is as follows. The capture antibody is reacted in a 96-well plate and washed with a washing buffer. The sample is treated at a concentration of 60 μM and allowed to react at room temperature for 2 hours. The detection antibody, HRP enzyme, substrate solution, and stop solution are then added in turn and reacted for the time indicated in the protocol, washing three times with each pass through each step . After the final reaction, the absorbance is measured at a wavelength of 450 nm using a spectrophotometer. The results are shown in Table 1 below.

Adiponectin expression level results matter Adiponectin (pg / ml, Avg ± SD) Untreated group 32 ± 11 IDX treated group 302 ± 50 IDX + glibenclamide 1832 ± 110 IDX + kojic acid (60 [mu] M) 312 ± 103 IDX + Example 1 (60 [mu] M) 1435 ± 113 IDX + Example 2 (60 [mu] M) 1300 + 140

The compounds of Examples 1 and 2 are koji acid ester compounds. According to the above Table 1, in the experiment for increasing the amount of adiponectin expression, kojic acid showed no effect, but the compounds of Example 1 and Example 2 increased the amount of adiponectin expression. In the examples according to the present invention, it can be confirmed that the amount of expression of climbenclide, which is a positive control, does not differ much, and thus the hydroxypiranone derivative compound or the composition comprising the same according to the present invention exhibits remarkable promotion of adipocyte differentiation And thus, it was confirmed that the effect of increasing skin volume or elasticity is exhibited.

Formulation examples of compositions according to one aspect of the present disclosure are described below, but are also applicable to various other formulations, which are intended to be illustrative only and not for purposes of limitation.

[Formulation Example 1] Soft capsule

8 mg of the hydroxypiranone derivative of Example 1 or 2, 9 mg of vitamin E, 9 mg of vitamin C, 2 mg of palm oil, 8 mg of vegetable hardening oil, 4 mg of yellow radish and 9 mg of lecithin were mixed and mixed according to a usual method to prepare a soft capsule filling liquid do. 400 mg per capsule is filled to prepare a soft capsule. Separately from the above, a soft capsule sheet was prepared in a ratio of 66 parts by weight of gelatin, 24 parts by weight of glycerin and 10 parts by weight of sorbitol solution, and filled with the filling solution to prepare a soft capsule containing 400 mg of the composition according to the present invention.

[Formulation Example 2] Tablets

8 mg of the hydroxypiranone derivative of Example 1 or 2, 9 mg of vitamin E, 9 mg of vitamin C, 200 mg of galactooligosaccharide, 60 mg of lactose and 140 mg of maltose were mixed and granulated using a fluid bed drier, ). 500 mg of these compositions are tabletted by conventional methods to prepare tablets.

[Formulation Example 3] Drinking agent

8 mg of the hydroxypiranone derivative of Example 1 or 2, 9 mg of vitamin E, 9 mg of vitamin C, 10 g of glucose, 0.6 g of citric acid and 25 g of liquid oligosaccharide were mixed and 300 ml of purified water was added to fill each bottle 200 ml each . It is filled in a bottle and sterilized at 130 ° C for 4 to 5 seconds to prepare a drink.

[Formulation Example 4]

8 mg of the hydroxypiranone derivative of Example 1 or 2, 9 mg of vitamin E, 9 mg of vitamin C, 250 mg of anhydrous crystalline glucose and 550 mg of starch were mixed and molded into granules using a fluidized bed granulator, .

[Formulation Example 5]

Injection was prepared according to a conventional method according to the composition shown in Table 2 below.

Compounding ingredient content The hydroxypiranone derivative of Example 1 or 2 10-50 mg Sterile sterilized water for injection Suitable amount pH adjusting agent Suitable amount

[Formulation Example 6] Health functional food

Health functional foods were prepared according to the compositions shown in Table 3 below by a conventional method.

Compounding ingredient content The hydroxypiranone derivative of Example 1 or 2 20 mg Vitamin A acetate 70 μg Vitamin E 1.0 mg Vitamin B1 0.13 mg Vitamin B2 0.15 mg Vitamin B6 0.5 mg Vitamin B12 0.2 μg Vitamin C 10 mg Biotin 10 μg Nicotinic acid amide 1.7 mg Folic acid 50 μg Calcium pantothenate 0.5 mg Ferrous sulfate 1.75 mg Zinc oxide 0.82 mg Magnesium carbonate 25.3 mg Potassium monophosphate 15 mg Dicalcium phosphate 55 mg Potassium citrate 90 mg Calcium carbonate 100 mg Magnesium chloride 24.8 mg

Although the composition ratio of the above-mentioned vitamin and mineral mixture is comparatively mixed with a component suitable for a health functional food as a preferred embodiment, the compounding ratio may be arbitrarily modified.

[Formulation Example 7] Health drinks

Health drinks were prepared in a conventional manner according to the composition shown in Table 4 below.

Compounding ingredient content The hydroxypiranone derivative of Example 1 or 2 1000 mg Citric acid 1000 mg oligosaccharide 100 g Taurine 1g Purified water Balance

The above components are mixed according to a conventional health drink manufacturing method, and the mixture is stirred and heated at 85 DEG C for about 1 hour, and then the solution is sterilized by filtration.

[Formulation Example 8] Flexible longevity (skin lotion)

The softening longevity was prepared by a conventional method according to the composition shown in Table 5 below.

Compounding ingredient Content (% by weight) The hydroxypiranone derivative of Example 1 or 2 0.2 glycerin 3.0 Butylene glycol 2.0 Propylene glycol 2.0 Carboxyvinyl polymer 0.1 Phage-12 nonylphenyl ether 0.2 Polysorbate 80 0.4 ethanol 10.0 Triethanolamine 0.1 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 9] Nutritional lotion (milk lotion)

Nutrition lotion was prepared according to a conventional method according to the composition shown in Table 6 below.

Compounding ingredient Content (% by weight) The hydroxypiranone derivative of Example 1 or 2 1.0 glycerin 3.0 Butylene glycol 3.0 Propylene glycol 3.0 Carboxyvinyl polymer 0.1 Wax 4.0 Polysorbate 60 1.5 Caprylic / capric triglyceride 5.0 Squalane 5.0 Sorbitacecequioleate 1.5 Liquid paraffin 0.5 Cetearyl alcohol 1.0 Triethanolamine 0.2 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 10] Nourishing cream

Nutritive creams were prepared according to the compositions listed in Table 7 below in a conventional manner.

Compounding ingredient Content (% by weight) The hydroxypiranone derivative of Example 1 or 2 2.0 glycerin 3.0 Butylene glycol 3.0 Liquid paraffin 7.0 Beta Glucan 7.0 Carbomer 0.1 Caprylic / capric triglyceride 3.0 Squalane 5.0 Cetearyl glucoside 1.5 Sorbitan stearate 0.4 Polysorbate 60 1.2 Triethanolamine 0.1 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 11] Massage cream

Massage creams were prepared in a conventional manner according to the composition shown in Table 8 below.

Compounding ingredient Content (% by weight) The hydroxypiranone derivative of Example 1 or 2 2.0 glycerin 8.0 Butylene glycol 4.0 Liquid paraffin 45.0 Beta Glucan 7.0 Carbomer 0.1 Caprylic / capric triglyceride 3.0 Wax 4.0 Cetearyl glucoside 1.5 Sesquioleic acid sorbitan 0.9 Vaseline 3.0 paraffin 1.5 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 12] Pack

Packs were prepared in a conventional manner according to the composition shown in Table 9 below.

Compounding ingredient Content (% by weight) The hydroxypiranone derivative of Example 1 or 2 0.2 glycerin 4.0 Polyvinyl alcohol 15.0 Hyaluronic acid extract 5.0 Beta Glucan 7.0 Allantoin 0.1 Nonyl phenyl ether 0.4 Polysorbate 60 1.2 Ethanol preservative 6.0 Preservative, coloring, fragrance Suitable amount Purified water Balance

Having described specific portions of the disclosure in detail, those skilled in the art will appreciate that these specific embodiments are merely exemplary and are not intended to limit the scope of the disclosure. Accordingly, the actual scope of the disclosure will be defined by the appended claims and their equivalents.

Claims (8)

A skin volume or elasticity-enhancing composition comprising a hydroxypiranone derivative represented by the following formula (1) as an active ingredient.
[Chemical Formula 1]

In the formula, R is -CH ₂ -, or -CH ₂ CH ₂ - Im. The composition of claim 1, wherein the composition promotes the differentiation of mesenchymal stem cells into adipocytes. The composition of claim 1, wherein the composition has a concentration of the active ingredient of 0.01 μM to 100 μM based on the total volume of the composition. The skin volume or elasticity-enhancing composition according to claim 1, wherein the composition increases fat tissue. 5. The composition according to any one of claims 1 to 4, wherein the composition is a pharmaceutical or cosmetic composition. A composition for promoting adipocyte differentiation comprising a hydroxypiranone derivative represented by the following formula (1) as an active ingredient.
[Chemical Formula 1]

In the formula, R is -CH ₂ -, or -CH ₂ CH ₂ - Im. The composition according to claim 6, wherein the composition promotes differentiation of mesenchymal stem cells into adipocytes. The composition according to claim 6, wherein the concentration of the active ingredient is 0.01 μM to 100 μM or more based on the total volume of the composition.

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